Triethylamine → HCID 87056047, compound

HRID 2201548Notes

Reaction equation

HRID 2201548 reaction equation
[F:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][NH:7][C:8](=[O:42])[C:9]2[C:14]([OH:15])=[CH:13][CH:12]=[C:11]([C:16]3[C:17]([N:36]([CH3:41])[S:37]([CH3:40])(=[O:39])=[O:38])=[CH:18][C:19]4[O:23][C:22]([C:24]5[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=5)=[C:21]([C:31](=[O:34])[NH:32][CH3:33])[C:20]=4[CH:35]=3)[N:10]=2)=[CH:4][CH:3]=1.CCN(CC)CC.Cl[C:53](Cl)([O:55]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:8](=[O:42])[C:9]3[N:10]=[C:11]([C:16]4[C:17]([N:36]([CH3:41])[S:37]([CH3:40])(=[O:38])=[O:39])=[CH:18][C:19]5[O:23][C:22]([C:24]6[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=6)=[C:21]([C:31]([NH:32][CH3:33])=[O:34])[C:20]=5[CH:35]=4)[CH:12]=[CH:13][C:14]=3[O:15][C:53]2=[O:55])=[CH:43][CH:44]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 117771656HCID 117771656, compound

Product 1

HCID 87056047HCID 87056047, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(4-fluorobenzyl)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-3-hydroxypicolinamide (30 mg, 0.05 mmol) and Et3N (11 mg, 0.10 mmol) in CH2Cl2 (5 mL) was stirred at RT under N2 atmosphere, and then triphosgene (18 mg, 0.06 mmol) was added portionwise. The mixture was stirred at RT for 4 h. The solvent was removed by rotary evaporator. After purified by prep-TLC (DCM:MeOH=60:1), 5-(3-(4-fluorobenzyl)-2,4-dioxo-3,4-dihydro-2H-pyrido[2,3-e][1,3]oxazin-6-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide was obtained. (15 mg, yield: 48%). 1H-NMR (CDCl3, 400 MHz) δ 7.97˜8.05 (m, 2H), 7.92 (m, 2H), 7.72 (d, J=8.4 Hz, 1H), 7.52˜7.63 (m, 3H), 7.19 (t, J=8.4 Hz, 2H), 7.01 (t, J=8.4 Hz, 2H), 6.14 (d, J=4.4 Hz, 1H), 5.20 (s, 2H), 3.24 (s, 3H), 2.98 (d, J=4.8 Hz, 3H), 2.95 (s, 3H). MS (M+H)+: 647.

Workup

  1. stirringThe mixture was stirred at RT for 4 h
  2. customThe solvent was removed by rotary evaporator
  3. customAfter purified by prep-TLC (DCM:MeOH=60:1)

Sources & evidence

ORD record
ord-adf8400e268f4d9f9a724859c9eeb561
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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